What happens when the practice you built starts feeling like a trap?
In this deeply honest Money Sessions episode, Tiffany sits down with therapist Hillary Pilotto to unpack the emotional, financial, and identity-level shifts that helped them go from exhausting $6K months to consistent $10K+ months… while seeing WAY fewer clients.
And here’s the thing:
Hillary already had what many therapists think they want.
A thriving group practice.
An associate.
An admin team.
Insurance referrals flowing in.
A “successful” business on paper.
But underneath?
They were overworking, overwhelmed, disconnected from their own life… and quietly realizing they didn’t actually want the business they had built.
This conversation is about what happens when you finally stop abandoning yourself to keep everyone else comfortable.
It’s about:
- Leaving insurance
- Letting yourself disappoint people
- Rebuilding your relationship with money
- Releasing “good therapist” conditioning
- Learning to trust your own desires
- And creating a business that actually supports your LIFE
And perhaps most importantly?
Hillary talks openly about the grief and fear that comes with changing — even when the change is exactly what you need.
Because no…
This process isn’t easy.
But it is possible.
Listen to the episode:
In this episode, Hillary shares:
- Going from 20+ sessions a week to just 10–13 clients
- Increasing fees to $280/session
- Why “successful on paper” can still feel deeply unsustainable
- The emotional labor of owning a group practice
- Leaving insurance despite fear, guilt, and external pressure
- Why so many therapists stay trapped at the $5K–$6K/month ceiling
- The difference between marketing strategy and mindset work
- How community support changed everything
- Releasing scarcity and stepping into abundance
- Building a practice around motherhood, spaciousness, and nervous system regulation
- The identity shifts required to charge Life First Fees
One of the most powerful moments in the episode?
When Hillary says:
“If I don’t want to do something anymore, I don’t question it or feel guilty. I just know… I don’t want to do that.”
WHEW.
If you’ve been secretly fantasizing about working less…
If you’ve built a practice that no longer fits your life…
If you’ve been telling yourself “this is just how private practice has to be”…
This episode will crack something open for you.
And if this episode hit you somewhere deep…
If you’re realizing you’ve been over-functioning, over-giving, and undercharging for far too long…
Email Tiffany directly at tiffany@leaninmakebank.com with the word READY.
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Resources mentioned
Connect with Hillary: Hillary@betterbalancecounseling.com
More about Hillary
I’m Hillary Pilotto, a certified EMDR therapist based near Chicago. I help adults in midlife, often parents or those in big life transitions, get unstuck, calm their nervous systems, and break the cycle of their upbringing.
